Please use this identifier to cite or link to this item:
http://dx.doi.org/10.25673/115575
Title: | Structural characterization of a 3-hydroxychromone dye trehalose conjugate for fluorescent labelling of mycobacteria |
Author(s): | Richter, Adrian Goddard, Richard W. Brinkmann, Lea Siersleben, Fabienne Seidel, Rüdiger W. |
Issue Date: | 2024 |
Type: | Article |
Language: | English |
Abstract: | 3-Hydroxychromone (3HC) dye trehalose conjugates have previously been exploited as environment-sensitive fluorescent labels to detect mycobacteria by fluorescence microscopy. We have studied the 3HC dye 2-(6-(diethylamino)benzofuran-2-yl)-3-hydroxy-4H-chromen-4-one (3HC-2) trehalose conjugate 3HC-2-Tre by X-ray crystallography, spectroscopic methods augmented by DFT calculations and conducted preliminary labelling experiments with Mycobacterium abscessus, a non-tuberculous mycobacterium and opportunistic pathogen. In the crystal structure of 3HC-2-Tre ⋅ 3.14 H2O, the 3HC-2-Tre molecules exhibit an intramolecular Osingle bondH⋅⋅⋅O hydrogen bond between the 5-hydroxy group of trehalose and the chromone carbonyl oxygen atom, and form hydrogen-bonded dimers via the trehalose units with approximate local C2 symmetry. The chromophore adopts an s-cis conformation of the chromone and benzofuran systems about its central Csingle bondC bond, as previously encountered in the crystal structure of the free dye 3HC-2, and the trehalose moieties approximately retain the shape as found in the crystal structures of anhydrous trehalose and the dihydrate. Absorption spectra of 3HC-2-Tre acquired in four different solvents revealed small positive solvatochromy. Fluorescence microscopy detected M. abscessus cells treated with 3HC-2-Tre in the GFP channel. |
URI: | https://opendata.uni-halle.de//handle/1981185920/117528 http://dx.doi.org/10.25673/115575 |
Open Access: | Open access publication |
License: | (CC BY-NC-ND 4.0) Creative Commons Attribution NonCommercial NoDerivatives 4.0 |
Journal Title: | Journal of molecular structure |
Publisher: | Elsevier |
Publisher Place: | New York, NY [u.a.] |
Volume: | 1298 |
Issue: | Part 2 |
Original Publication: | 10.1016/j.molstruc.2023.137010 |
Page Start: | 1 |
Page End: | 8 |
Appears in Collections: | Open Access Publikationen der MLU |
Files in This Item:
File | Description | Size | Format | |
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1-s2.0-S0022286023021002-main.pdf | 6.34 MB | Adobe PDF | View/Open |